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WO1999005572A3 - Viscosity stabilization of radiation-curable compositions - Google Patents

Viscosity stabilization of radiation-curable compositions Download PDF

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Publication number
WO1999005572A3
WO1999005572A3 PCT/EP1998/004284 EP9804284W WO9905572A3 WO 1999005572 A3 WO1999005572 A3 WO 1999005572A3 EP 9804284 W EP9804284 W EP 9804284W WO 9905572 A3 WO9905572 A3 WO 9905572A3
Authority
WO
WIPO (PCT)
Prior art keywords
radiation
composition
viscosity
polymerization
curable compositions
Prior art date
Application number
PCT/EP1998/004284
Other languages
French (fr)
Other versions
WO1999005572A2 (en
Inventor
Anastasios Panayioti Melisaris
Stephen Duncan Hanna
Thomas Hsing Pang
Original Assignee
Ciba Geigy Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Priority to CA002296587A priority Critical patent/CA2296587A1/en
Priority to JP2000504488A priority patent/JP4614030B2/en
Priority to BR9811801-3A priority patent/BR9811801A/en
Priority to AU88599/98A priority patent/AU751062B2/en
Priority to EP98940197A priority patent/EP0998696A2/en
Priority to KR1020007000410A priority patent/KR20010021846A/en
Priority to IL13310898A priority patent/IL133108A/en
Publication of WO1999005572A2 publication Critical patent/WO1999005572A2/en
Publication of WO1999005572A3 publication Critical patent/WO1999005572A3/en
Priority to NO20000264A priority patent/NO20000264L/en

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0037—Production of three-dimensional images
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
    • B29C64/129—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask
    • B29C64/135—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask the energy source being concentrated, e.g. scanning lasers or focused light sources
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y10/00—Processes of additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y30/00—Apparatus for additive manufacturing; Details thereof or accessories therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B33Y70/10—Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C08J3/243—Two or more independent types of crosslinking for one or more polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0094—Condition, form or state of moulded material or of the material to be shaped having particular viscosity
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/06—Condition, form or state of moulded material or of the material to be shaped containing reinforcements, fillers or inserts
    • B29K2105/16—Fillers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Structural Engineering (AREA)
  • Composite Materials (AREA)
  • Civil Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)
  • Polymerisation Methods In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to a process for the production of three-dimensional articles by stereolithography using a radiation-curable composition comprising a mixture of at least one cationically polymerizable compound and/or at least one free radical polymerizable compound, at least one filler material and at least one photoinitiator for cationic and/or radical polymerization. An organic viscosity stabilizer material may be brought into contact with the composition to substantially delay or prevent undesirable viscosity increase and subsequently premature polymerization. A filler material is optionally added to the composition in an effective amount to at least delay or prevent a significant increase in viscosity and polymerization. The process is particularly suitable for stabilizing resins in stereolithography baths. The present invention also relates to cured articles resulting from said process and a process for manufacturing said radiation-curable compositions and stabilized compositions resulting therefrom.
PCT/EP1998/004284 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable compositions WO1999005572A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002296587A CA2296587A1 (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable compositions
JP2000504488A JP4614030B2 (en) 1997-07-21 1998-07-10 Radiation-Viscosity stabilization of curable compositions
BR9811801-3A BR9811801A (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation curable compositions.
AU88599/98A AU751062B2 (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable filled compositions
EP98940197A EP0998696A2 (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable filled compositions
KR1020007000410A KR20010021846A (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable filled compositions
IL13310898A IL133108A (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable filled compositions
NO20000264A NO20000264L (en) 1997-07-21 2000-01-19 Viscosity stabilization of radiation curable filled compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US5331397P 1997-07-21 1997-07-21
US60/053,313 1997-07-21

Publications (2)

Publication Number Publication Date
WO1999005572A2 WO1999005572A2 (en) 1999-02-04
WO1999005572A3 true WO1999005572A3 (en) 1999-04-15

Family

ID=21983353

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/004284 WO1999005572A2 (en) 1997-07-21 1998-07-10 Viscosity stabilization of radiation-curable compositions

Country Status (12)

Country Link
US (2) US6099787A (en)
EP (1) EP0998696A2 (en)
JP (2) JP4614030B2 (en)
KR (1) KR20010021846A (en)
AU (1) AU751062B2 (en)
BR (1) BR9811801A (en)
CA (1) CA2296587A1 (en)
IL (1) IL133108A (en)
NO (1) NO20000264L (en)
TW (1) TW396296B (en)
WO (1) WO1999005572A2 (en)
ZA (1) ZA986424B (en)

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JP4350832B2 (en) * 1999-04-19 2009-10-21 Ｊｓｒ株式会社 Photocurable resin composition for three-dimensional modeling and a modeled product obtained by curing the same
US20030207959A1 (en) * 2000-03-13 2003-11-06 Eduardo Napadensky Compositions and methods for use in three dimensional model printing
US8481241B2 (en) 2000-03-13 2013-07-09 Stratasys Ltd. Compositions and methods for use in three dimensional model printing
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US8086336B2 (en) * 2002-09-30 2011-12-27 Medical Modeling Inc. Method for design and production of a custom-fit prosthesis
US20040087687A1 (en) * 2002-10-30 2004-05-06 Vantico A&T Us Inc. Photocurable compositions with phosphite viscosity stabilizers
US8338074B2 (en) * 2003-06-25 2012-12-25 Cmet Inc. Actinic radiation-curable stereolithographic resin composition having improved stability
ATE533611T1 (en) * 2003-07-23 2011-12-15 Dsm Ip Assets Bv RADIATION CURED RESIN COMPOSITION WITH REDUCABLE VISCOSITY
JP2007513234A (en) * 2003-12-02 2007-05-24 ディーエスエム アイピー アセッツ ビー．ブイ． Flame retardant radiation curable composition
CA2557226A1 (en) * 2004-03-22 2005-10-06 Huntsman Advanced Materials (Switzerland) Gmbh Photocurable compositions
US20060172230A1 (en) * 2005-02-02 2006-08-03 Dsm Ip Assets B.V. Method and composition for reducing waste in photo-imaging applications
US7696260B2 (en) * 2006-03-30 2010-04-13 Dsm Ip Assets B.V. Cationic compositions and methods of making and using the same
US8738166B2 (en) * 2009-02-24 2014-05-27 Panasonic Corporation Method for manufacturing three-dimensional shaped object and three-dimensional shaped object obtained by the same
US10493689B1 (en) * 2010-09-02 2019-12-03 The Boeing Company Methods for forming thermoplastic parts with freeform tooling
IT1403482B1 (en) * 2011-01-18 2013-10-17 Dws Srl METHOD FOR THE PRODUCTION OF A THREE-DIMENSIONAL OBJECT AND A STEREOLITHOGRAPHIC MACHINE USING THIS METHOD
CN104610511B (en) 2013-11-05 2018-11-16 帝斯曼知识产权资产管理有限公司 Stable matrix-filled liquid radiation-curable resin composition for additive manufacturing
JP2016010870A (en) * 2014-06-27 2016-01-21 セイコーエプソン株式会社 Method for manufacturing three-dimensional molded article and three-dimensional molded article
US9650526B2 (en) * 2014-09-09 2017-05-16 3D Systems, Inc. Method of printing a three-dimensional article
CN107428092B (en) * 2015-03-19 2021-06-08 陶氏环球技术有限责任公司 Additive manufacturing method using light-regulated free radical polymerization
WO2018119049A1 (en) 2016-12-20 2018-06-28 Basf Se Photopolymer ceramic dispersion for additive fabrication
WO2018119067A1 (en) 2016-12-20 2018-06-28 Basf Se Photopolymer ceramic dispersion
TW201840964A (en) 2016-12-20 2018-11-16 德商巴地斯顏料化工廠 Method for determining an amount of sediment in a ceramic dispersion
US9899758B1 (en) * 2017-01-25 2018-02-20 Delphi Technologies, Inc. Electrical connector system with enhanced terminal retaining beam
CN110198827B (en) * 2017-03-06 2021-09-21 麦克赛尔控股株式会社 Ink set for mold material, support material composition, ink set, three-dimensional object, and method for producing three-dimensional object
CN110520232A (en) 2017-03-28 2019-11-29 福特全球技术公司 Stable increasing material manufacturing product
WO2019169211A1 (en) * 2018-03-02 2019-09-06 Formlabs, Inc. Latent cure resins and related methods

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WO1990004211A1 (en) * 1988-10-11 1990-04-19 Desoto, Inc. Synergistic initiator compositions for the visible light fabrication and postcure of stereolithographic objects
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WO1990001512A1 (en) * 1988-08-12 1990-02-22 Desoto, Inc. Photo-curable vinyl ether compositions
WO1990004211A1 (en) * 1988-10-11 1990-04-19 Desoto, Inc. Synergistic initiator compositions for the visible light fabrication and postcure of stereolithographic objects
US5236812A (en) * 1989-12-29 1993-08-17 E. I. Du Pont De Nemours And Company Solid imaging method and apparatus
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Also Published As

Publication number Publication date
NO20000264D0 (en) 2000-01-19
TW396296B (en) 2000-07-01
KR20010021846A (en) 2001-03-15
JP2010214960A (en) 2010-09-30
IL133108A (en) 2003-07-06
ZA986424B (en) 1999-01-21
EP0998696A2 (en) 2000-05-10
NO20000264L (en) 2000-01-19
JP2001511425A (en) 2001-08-14
IL133108A0 (en) 2001-03-19
JP4884548B2 (en) 2012-02-29
AU751062B2 (en) 2002-08-08
US6350403B1 (en) 2002-02-26
WO1999005572A2 (en) 1999-02-04
AU8859998A (en) 1999-02-16
CA2296587A1 (en) 1999-02-04
JP4614030B2 (en) 2011-01-19
BR9811801A (en) 2000-09-19
US6099787A (en) 2000-08-08

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